Wearing ankle boots with skirts and dresses

Last weekend, not the one just gone but the one before, I spent the majority of the weekend working at home or going out to eat. Well, other than the night I spent in the wilderness without phone reception, but THAT is another story. And I was pretty darn excited to get to wear my ankle boots for one of the first times this season. Win.

Cooler weather is coming. Ankle boot weather. Apparently, we certainly haven’t seen much of it. Even Melbourne didn’t turn it on for me while I was there. But since I am well-adjusted to not exactly getting ‘boots’ weather I just do what I do best and wear my boots with skirts and dresses. Easy.

You do that too right? Wear your ankle boots with skirts and dresses? 

I blame the 90’s and the whole Doc Martins and floral dresses thing. I mean, who didn’t want to be Drew or Liv or Winona or one of those cool chicks stomping around looking like a delicate flower/crusher of things. I know I did. 90’s girl DREAM.

But how do you make it work?

First some pics, of this cute trans-seasonal outfit and then let’s talk about wearing ankle boots with skirts and dresses as a plus size woman.  Things I’ve learnt and tricks to make you more comfortable if you feel like it has just never worked for you.

Right, I have a few key points about making ankle boots with skirts and dresses work. Because I love the combination and think if you want to wear it, you darn well should. But a lot ladies have reservations. Especially if they are plus size and feel like their legs now look like tree trunks. If that’s you and nothing you’ve found seems to work let’s talk things to look for. I’m sure you’re ready to hear this, right?

Look for loose at the ankle or a DIP at the front.

My old nude boots, oh man I miss those poor broken babies, are a perfect example of this (see link). They dip at the front and help elongate the leg and slim the ankle. If you can’t find a pair that dips, find a pair that is wide at the ankle. Sure a slim fit may seem like the better idea, but it will just make your legs look SQUISHED in there. Go for a wide ankle width like from brands like Autograph or City Chic.

If you’re afraid of looking stumpy, go nude.

HA. That was fun to write. You could go nude, or you could choose some nude boots. I’m a fan of my blonde coloured nude boots (especially when I AM blonde) because they just bookend my outfits so easily. But the main advantage is that like nude heels, they will elongate the leg and let you build up to something more out there. Wait, did I mention my nude boots? I did. Sigh. Here they are looking amazing again.

Always always have a chunky heel.

I knoooow, you love the riding boot style, the flat soft boot. Well if you’re ankle boot game is a little weak you need the heel for oomph. And I suggest chunky because you don’t lose any of the comfort of a flat. Well, not much of it anyway. Another alternative is a wedge, like this boot I picked up from Target a while back.

Try stockings or tights.

Sometimes all it takes to get into your ankle boots with skirts groove is a pair of tights or stockings. I did this outfit a while ago that paired black boots with black stockings and it makes for a smooth transition into the boot game.

Wearing Stripe Top from 17 Sundays (similar’ish top), Button Up Skirt from ASOS Curve (current), Ankle boots from Autograph Fashion (last season) and bemused expression from the combined effect of my hair and the wind… Gosh. 

Got any plus size woman type ankle boot wearing tips? I’d love to hear them.